Mindy Kaling’s Dos & Don’ts of Dressing for Awards Shows

I hate gowns. I hate them. It’s weird. I love fashion, but I never, even as a chubby Indian kid, wanted to look like a fairy princess. I’d rather look cool and hot than elegant and beautiful. I recognize these preferences are the result of self-preservation, because I have much more of a fighting chance to look cool or hot in jeans and a button-down than elegant and beautiful in some long gown with a train. I mean, when you think of me, what do you picture? Me in a flowing gown, dripping in jewelry on the red carpet? Or me in jeans and a pink hoodie, watching Real Housewives on the sofa, eating licorice? Don’t answer. It’s so obvious what the answer is.

One of my best qualities is that I’m truly open to anything fashion-wise. One of my worst is that my skin is incredibly thin to criticism. These two traits do battle anytime I get dressed for a red-carpet event. In honor of the Oscars, let me take you on a little tour of my recent history.

My Fashion Police moment

Let’s look, for instance, at the dress I wore to the 2010 Emmys, at right, when I was co-nominated for best comedy writing with my boss Greg Daniels. Because there was a possibility I might go onstage, I hired a stylist to help me. Hiring a stylist basically means you go to an agency’s website and look at pictures of celebrities and models wearing outfits that the stylist has assembled. This activity in itself is a complete joy, obviously.

I picked a stylist I’ll call Liza. She was an impossibly thin Debbie Harry look-alike who wore six-inch platform sandals. Liza arrived at my house on a Saturday morning with four racks containing hundreds of thousands of dollars’ worth of gowns, jewelry and shoes. It was magical. They were just sitting there, all on the same wood floor where I played Rock Band badly.

Trying on gowns is demoralizing. I’m smaller on top than I am on the bottom, so gowns rarely fit me well. So I picked my dress because it was easy to dance in. I figured if we won, I’d dance up a storm. I also wanted to look edgy and young, reveal some leg and showcase these gorgeous (and disgustingly expensive) Alexander McQueen shoes, which were black with purple rhinestones and had a heart-shaped toe opening. Usually for red-carpet events, I spend a sickening amount on shoes that remain hidden under the gown, and I’m like, “Why didn’t I just go to Aldo and buy $50 pumps? This is nuts.” Not this time!

By the time I was in the limo with my best friend, Brenda, I started suspecting the dress was a mistake: Brenda couldn’t sit within three feet of me, because my dress took up the whole area. (At the ceremony, it overflowed into Greg’s seat, where he kept pushing it back until finally, he gave up, letting it cover his lap.) Yikes, right? In retrospect, it’s pretty amazing that I messed up a black dress. I usually don’t like to wear them because I think black is boring. Maybe because it’s the signature style of Supreme Court justices. Basically, you’re saying, “Don’t think of me sexually! I want to blend in.” Black dresses might be flattering and confidence-giving, but they are never memorable, unless you’re Angelina Jolie, in which case you could wear a Supreme Court robe and steal away a million husbands.

But this little number does have historical significance. It inaugurated me into the club of people who’ve been mocked on the E! show Fashion Police, led by the reanimated corpse of Joan Rivers, who’s actually a very funny old bag of bones. She said I looked like I’d fallen out of Patti LaBelle’s nose and that I was wearing Snooki’s old prom dress. Even though it made me cry later that night, I had to admit that it was a funny thing to say.

Right after Joan skewered me, I promised myself I’d wear only boring black shifts. But then a month after, I caught an episode of Fashion Police while I was working out at the gym. The judges just seemed kind of pitiful, and I thought, If anyone is going to scare me into dressing a certain way, it’s going to be someone formidable. So I stopped caring. Let the Fashion Police dis my outfits. I make my living taking risks and being creative; they make theirs scrutinizing creativity. Which would you rather do?

My Golden Globes success story

Canary yellow is my favorite color. Most people think it’s pink, because pink is the favorite of my character, Kelly, on The Office. And believe me, I have a deep, personal relationship with pink. But nothing gets me more excited than rocking deep canary yellow.

So as soon as I saw this Gucci gown (left), I knew I had to wear it to the 2009 Golden Globes. It was a little tight in the hips, so I spent the next three weeks running intervals on the treadmill and eating lean proteins and vegetables, with a handful of berries as my “treat.” It was a pathetic and unhappy time during which I was endlessly grouchy. I recommend it to no one. But it was worth it for the gown.

It is one of my favorite looks. I love one-shoulder gowns, even though this is the cut of choice for every Real Housewife, whether she’s throwing her toddler an insanely elaborate birthday party or going to get a face-lift.

My close friend and Office costar Ellie Kemper got ready for the Golden Globes with me. We got our hair and makeup done at my house while listening to a mix I made that was simply alternating Rihanna and Beyoncé songs. (Why would you listen to anything else?) We ate sushi, drank champagne and walked around in Spanx without feeling embarrassed.

The gown cost serious money, and I don’t think I’ll ever wear it again, but I love it. Quentin Tarantino told me I looked pretty that night, so now I call it the Tarantino dress. I’m annoyed that the only photo I have of me in the Tarantino is in front of a dreadful black plastic backdrop that seems to be made entirely of garbage bags. But my body looks slammin’, and I’m smiling, and that’s all that matters.

Speaking of which: the smiling conundrum. I have wonky teeth, full of gaps, and I always tell myself to do a classy, closemouthed smile, but in the end, I don’t have the willpower. I can’t help it. I mean, I’m literally on a Hollywood red carpet. That chubby Indian kid in me is beaming so hard I can’t not smile. I’ll just have to leave the cool “Why are you bothering me?” beauty scowl to Victoria Beckham.

Arm warmers: always a Don’t

Sometimes there are red-carpet events for things that aren’t even fancy. I was invited to a premiere for a car once (I know, I don’t really get it either), and this is what I wore, above.

I think this is an all-time low in my fashion history. The neon yellow scarf is a disaster, obviously, and the gold bag is confusing (I think it’s technically a free makeup bag I got for buying $50 worth of products), but the arm warmers are the real travesty. Since I’m wearing short sleeves, the arm warmers are clearly there only for fashion, not function. And what is this look I’m trying to pull off? Vampire hipster clown? I plan on showing this picture to my future children to remind them that even though Mom is perfect now, she came from humble origins. I also learned an important style lesson from this: Simple is best. Almost always.

“This wins ‘best clothing ensemble’ in the awards show of my heart.” —Kaling at the 2011 Screen Actors Guild Awards

My red-carpet triumph

To leave you on a positive note, and so you think of me as a generally attractive and put-together human, I’m ending this with the red-carpet look I’m most proud of. It’s from the 2011 Screen Actors Guild Awards.

Like every other American, I spend a good part of my time looking at Kardashians. Love or hate them, I think they dress phenomenally, which is sometimes tricky given their curves. So I tracked down their stylist, Monica Rose, to see if she’d style me. Monica is incredibly busy with the Kardashians, but she agreed to because she thought I was a hilarious and hot new voice in Hollywood (at least that’s what I assume; she never said this to me).

Monica arrived with racks of gowns. The interesting thing was that Monica, while completely versed in couture, is not a label snob. There were labels I’d never heard of, and also labels available at the suburban Macy’s where I grew up. I was immediately angry about this. I want to wear Elie Saab like Halle Berry, or Marchesa like Nicole Richie! I don’t want to look like the mall rat I secretly am!

I was wrong. Through Monica I learned that labels are fine but fit is paramount. She loved the color and the fabric, and reworked this Tadashi Shoji dress with a tailor so it fit me perfectly. We had three tailoring sessions because it was that important to her. I’m nervous about wearing light colors on my bottom half (a common concern for women with my body shape), but Monica freed me of that fear. The final touch: She cinched my waist in with a custom-made metal belt.

The Office didn’t win “best ensemble” that night; Modern Family did. But I, Mindy Kaling, won “best clothing ensemble” in the awards show of my heart. Yep, truly. Nailed it.